CN114456800B - Preparation method and application of perovskite quantum dot-molecular imprinting fluorescent coding microsphere for detecting sudan red I - Google Patents
Preparation method and application of perovskite quantum dot-molecular imprinting fluorescent coding microsphere for detecting sudan red I Download PDFInfo
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Abstract
The invention belongs to the technical field of fluorescent sensing material preparation and food safety detection, and particularly relates to a preparation method and application of perovskite quantum dot-molecular imprinting fluorescent coding microspheres for detecting sudan red I. According to the invention, perovskite quantum dots are used as fluorescent elements, a molecularly imprinted polymer is used as an encoding matrix, and a fluorescent encoding technology is adopted to prepare perovskite quantum dot-molecularly imprinted fluorescent encoding microspheres; the preparation method simplifies the preparation process, enhances the stability of the perovskite quantum dots, constructs a fluorescence sensing system by using the obtained fluorescence coding microsphere, and realizes the rapid quantitative analysis of the Sudan I in the chilli powder, chilli oil, tomato sauce, eggs and duck eggs.
Description
Technical Field
The invention belongs to the technical field of fluorescent sensing material preparation and food safety detection, and particularly relates to a preparation method and application of perovskite quantum dot-molecular imprinting fluorescent coding microspheres for detecting sudan red I.
Background
Perovskite quantum dots are novel fluorescent materials newly developed in recent years, and compared with other fluorescent materials, the perovskite quantum dots have the advantages of high quantum yield, high defect tolerance, tunable band gap and the like. However, perovskite quantum dots show strong instability in the environment of air, high temperature, high humidity or strong light irradiation, and the current application is mainly concentrated in the fields of solar cells, light emitting diodes and the like, and the application in the field of food detection is very few. Among the presently disclosed methods, although some rely on the selectivity of fluorescent materials for targets, the selectivity is not apparent, especially for similar species of similar structure and properties. Meanwhile, the diversity and complexity of food matrixes easily influence the accuracy of detection results, and false positive results are caused.
The presence of molecularly imprinted polymers (Molecular imprinting polymer, MIP) based on antigen-antibody specific binding can exactly compensate for the defect that fluorescent materials cannot specifically recognize targets. The perovskite quantum dot fluorescent molecularly imprinted polymer has great development potential in the field of harmful substance detection in foods in theory by combining the specific recognition of the molecularly imprinted polymer and the excellent fluorescence performance of the perovskite quantum dot. However, the method is limited by the instability of perovskite quantum dots, in order to ensure the stability and compatibility of the quantum dots in a reaction solvent in the preparation process, very complex modification processes are required to be carried out on the quantum dots, so that the experimental process is more complicated, and the layer-by-layer modification has great influence on the fluorescence intensity of the fluorescent material.
The quantum dot fluorescent coding technology is proposed to use polystyrene microsphere as a coding matrix, and fix the quantum dot inside the polystyrene microsphere by utilizing the swelling property of the polystyrene microsphere in chloroform and depending on the hydrophobic interaction between the microsphere and the quantum dot. In the process, the synthesis and the coding process of the polymer are separated and are not mutually interfered, the preparation process is not influenced by the polarity and the synthesis system of the quantum dots, the complex modification process of the quantum dots is not needed, and the method is simple and easy to use.
Sudan red I present in foods is an important factor in causing food safety problems. Sudan red I is an artificially synthesized industrial dye and is often used as a colorant for products such as perfumed soap, floor wax, oil and the like. Sudan red I has proved to have potential carcinogenicity to human body. The international cancer research institute lists sudan red i as the tertiary carcinogen. In the actual detection of sudan red I, the following two problems need to be solved at present: (1) In the detection process, sudan red usually remains in very complex samples of food matrixes such as chilli sauce, chilli powder, duck eggs and the like, and the accuracy of detection results is greatly influenced by interferents in the matrixes; (2) In the detection means, the chromatography is still the main method, the steps are complex, the flow is complex, the requirement of rapid detection cannot be met, and especially sudden food safety events can be met. Therefore, it is necessary to provide a high-efficiency and rapid detection means for sudan I in complex foods.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of perovskite quantum dot-molecular imprinting fluorescent coding microspheres for detecting sudan red I, and also provides application of the perovskite quantum dot-molecular imprinting fluorescent coding microspheres obtained by the preparation method in quantitative detection of sudan red I in foods.
According to the invention, perovskite quantum dots are used as fluorescent elements, a molecularly imprinted polymer is used as an encoding matrix, and a fluorescent encoding technology is adopted to prepare perovskite quantum dot-molecularly imprinted fluorescent encoding microspheres. The molecular engram polymer with specific adsorptivity to Sudan red I is synthesized by adopting a precipitation polymerization mode by taking Sudan red I as a template molecule. Then mixing and oscillating the polymer and the perovskite quantum dots to enable the quantum dots to enter the polymer, so that the polymer is endowed with excellent fluorescence performance, and the method separates a polymerization process from a fluorescence coding process, so that the perovskite quantum dots are effectively loaded on the molecularly imprinted polymer.
One of the purposes of the invention is to solve the compatibility of the perovskite quantum dot and the reaction system, effectively avoid the influence of a polymerization system on the fluorescence performance of the perovskite quantum dot, and simultaneously improve the stability of the perovskite quantum dot in the practical application process by utilizing the protection effect of the molecularly imprinted polymer on the perovskite quantum dot. The invention develops a preparation method of perovskite quantum dot-molecular imprinting fluorescent coding microspheres applicable to different emission wavelengths, and the method has universality on the perovskite quantum dots with different emission wavelengths.
The second object of the invention is to develop a rapid quantitative detection method suitable for sudan I in complex food substrates. Experiments prove that after encoding, the obtained fluorescent encoding microsphere still has good selectivity to template molecule Sudan red I, and the fluorescent sensing system constructed by the fluorescent encoding microsphere can be used for quantitative analysis of Sudan red I in chilli powder, chilli oil, tomato sauce, eggs and duck eggs. The method can be used for quantitative analysis of Sudan red I in food, can be extended to detection of other harmful substances in food, and has a certain practical significance.
The technical scheme of the invention is as follows:
a preparation method of perovskite quantum dot-molecular imprinting fluorescent coding microsphere for detecting sudan red I comprises the following steps:
(1) Dissolving 0.1mmol of sudan I serving as a template molecule in 20mL of pore-forming agent acetonitrile, adding 4mmol of functional monomer methacrylic acid and 2mmol of cross-linking agent, adding 20mg of initiator azo-diisobutyronitrile, performing ultrasonic dissolution, introducing nitrogen to deoxidize for 15min, immediately sealing, stirring at 60 ℃ for reaction for 24h, thermally initiating a formed polymerization system, and synthesizing by a precipitation polymerization method to obtain a polymer;
(2) Grinding the polymer, eluting with a mixed solution of methanol and acetic acid by a Soxhlet extraction method, removing template molecules, washing to neutrality by methanol, and drying to constant weight at 60 ℃ to obtain a Sudan red I molecularly imprinted polymer;
(3) Fluorescent coding: accurately absorbing 50 mu L of perovskite quantum dots, adding the perovskite quantum dots into 1mL of normal hexane, adding 10mg of Sudan red I molecularly imprinted polymer after ultrasonic homogenization, dissolving the polymer by ultrasonic, oscillating for 30min for fluorescent coding, washing, and drying at room temperature to obtain the perovskite quantum dot-molecularly imprinted fluorescent coding microsphere.
Preferably, in (1), the crosslinking agent is ethylene glycol dimethacrylate and divinylbenzene, and the molar ratio of the two is 1:1, a step of;
preferably, in (2), the volume ratio of the mixed solution of methanol and acetic acid is 8:2;
preferably, in (3), the perovskite quantum dot is CsPbBr 3 Quantum dot CsPbCl 1.5 Br 1.5 Quantum dot and CsPbI 2 At least one of the Br quantum dots.
Furthermore, the invention also provides application of the perovskite quantum dot-molecularly imprinted fluorescent coding microsphere in detecting the content of sudan I in foods, including but not limited to seasonings (such as chilli powder, chilli oil and tomato sauce) and eggs (such as eggs and duck eggs).
The invention has the beneficial effects that:
(1) The invention fully plays the synergistic effect of the molecular engram polymer with specific adsorptivity and the perovskite quantum dot, and simultaneously realizes the superior fluorescence performance of the polymer and the good stability of the perovskite quantum dot;
(2) According to the invention, a step method is used for preparing perovskite quantum dot-molecular imprinting fluorescent coding microspheres, firstly, a precipitation polymerization method is adopted for synthesizing a molecular imprinting polymer, and after synthesis is completed, the perovskite quantum dot and the molecular imprinting polymer are directly mixed and oscillated for coding, so that the influence of a polymerization system on the performance of the perovskite quantum dot is solved, the defect that the detection sensitivity is reduced due to the fact that the perovskite quantum dot is wrapped by the polymer during polymerization is overcome, and the detection efficiency is further improved;
(3) According to the perovskite quantum dot-molecular imprinting fluorescent coding microsphere, the specificity of the molecular imprinting polymer is utilized, so that the rapid quantitative analysis of sudan I in chilli powder, chilli oil, tomato sauce, eggs and duck eggs is realized, and a novel detection mode is provided for a rapid food safety detection method.
Drawings
FIG. 1 shows MIP@CsPbBr 3 A fluorescence coding microsphere preparation flow chart, wherein (a) is a molecular imprinting polymer preparation process and (b) is a fluorescence coding process;
FIG. 2 shows MIP@CsPbBr 3 Fluorescent coding microsphere and CsPbBr 3 The quantum dots irradiate fluorescent intensity for different time under ultraviolet (lambda=365 nm);
FIG. 3 shows MIP@CsPbBr 3 CsPbBr after washing fluorescent coding microsphere with normal hexane solution 3 Leakage rate of quantum dots.
Detailed Description
The present invention will now be further described in connection with specific embodiments in order to enable those skilled in the art to better understand the invention.
Example 1
Taking a preparation method of perovskite quantum dot-molecular imprinting fluorescent coding microsphere for detecting sudan red I as an example, the preparation method comprises the following steps:
(1) Sucking 20mL of acetonitrile into a 50mL round-bottom flask, adding 0.1mmol of sudan I into the round-bottom flask, dissolving the mixture by ultrasonic, adding 1mmol of ethylene dimethacrylate and 1mmol of divinylbenzene into the round-bottom flask as a cross-linking agent, finally adding 20mg of initiator azodiisobutyronitrile into the round-bottom flask, completely dissolving the initiator by ultrasonic, introducing nitrogen to remove oxygen for 15 minutes, immediately sealing the round-bottom flask, heating the round-bottom flask in a water bath at 60 ℃ for 24 hours, filtering the obtained polymer by using acetonitrile after precipitation polymerization is finished, and drying the polymer in an oven at 60 ℃ for 24 hours;
(2) Grinding the dried polymer, eluting the obtained polymer with a mixed solution of methanol and acetic acid (volume ratio is 8:2) in a Soxhlet extraction device to remove template Sudan red I, washing with methanol to neutrality, and drying in an oven at 60 ℃ for 24 hours to obtain a Sudan red I molecularly imprinted polymer;
(3) 1mL of n-hexane and 50. Mu.L of CsPbBr 3 Adding the quantum dot solution into a 2mL centrifuge tube, adding 10mg of molecularly imprinted polymer after ultrasonic mixing, dissolving the polymer by ultrasonic, and oscillating for 30 minutes; centrifuging to remove supernatant (10000 rpm,10 min), washing with n-hexane until no quantum dot is present in the supernatant, and drying at 25deg.C to obtain MIP@CsPbBr 3 The preparation process of the fluorescent coding microsphere is shown in figure 1.
Example 2
Regarding the stability evaluation of perovskite quantum dot-molecularly imprinted fluorescence encoded microspheres in example 1 described above, the procedure was as follows:
with MIP@CsPbBr in example 1 3 For example, the physical and chemical stability of the obtained fluorescent encoded microspheres were evaluated:
(1)MIP@CsPbBr 3 fluorescent coding microsphere and CsPbBr 3 Quantum dots at 365nm respectivelyIrradiating for 24h under an ultraviolet lamp, and measuring the fluorescence intensity under different irradiation times (0, 1, 2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 22 and 24 h);
(2) 1mg of MIP@CsPbBr 3 Adding the fluorescent coding microsphere into 1mL of n-hexane, performing centrifugation (10000 rpm,10 minutes) after ultrasonic treatment for 10 minutes, collecting supernatant and fluorescent coding microsphere, redispersing the fluorescent coding microsphere in 1mL of n-hexane, testing fluorescent intensity of the fluorescent coding microsphere and supernatant by using a fluorescent spectrophotometer, and obtaining CsPbBr in the n-hexane of the supernatant 3 The ratio of the fluorescence intensity of the quantum dots to the fluorescence intensity of the quantum dots in the microsphere represents the leakage amount, and the steps are repeated for 8 times.
As can be seen from FIG. 2, csPbBr after 24 hours of continuous irradiation 3 The fluorescence intensity of the quantum dot is obviously reduced to 18.54% of the initial value, and MIP@CsPbBr 3 The fluorescence-encoded microsphere has no obvious decrease in fluorescence intensity due to the protection effect of the encoded matrix molecularly imprinted polymer, and is still more than 95.08% of the initial value.
FIG. 3 is MIP@CsPbBr 3 The leakage rate of the quantum dots after the fluorescent coding microspheres are washed by the n-hexane solution for different times is 0.3 percent after 8 times of circulation, because the molecularly imprinted polymer has various functional groups and CsPbBr 3 Non-covalent interactions (such as hydrophobic interactions, electrostatic interactions and the like) exist among the quantum dots, and CsPbBr can be ensured 3 The quantum dots are firmly combined in the molecularly imprinted polymer, so that the leakage of the quantum dots is effectively avoided, and the stability and the accuracy of the detection method can be improved.
Example 3
With MIP@CsPbBr 3 The fluorescent coding microsphere is used as a fluorescent sensing system to verify the application in actual samples.
Taking five samples of chilli powder, chilli oil, duck eggs, eggs and tomato sauce as actual samples, respectively weighing 1g or 1mL of the samples, adding the samples into 10mL of n-hexane, ultrasonically extracting for 5min, centrifuging at 10000rpm for 10min, taking a supernatant, repeating the steps twice, merging the supernatant, blowing nitrogen to be nearly dry, and re-dissolving the supernatant again by using 10mL of n-hexane. 1mL of the treated sample extract was taken and 1mg of MIP@CsPbBr was added thereto 3 The fluorescent coded microspheres were shaken for 30 minutes at room temperature, and after sufficient reaction, the fluorescence intensity of each group of sample solutions was tested using a fluorescence spectrophotometer.
From the measurement, it can be seen from table 1 that the recovery rate of the labeled sample is 93.43% -108.46%, and the relative standard deviation is 2.8% -8.6%. The results show that MIP@CsPbBr 3 The fluorescent coding microsphere has reliability and practicability for analysis of the Sudan I in the labeled sample, has higher accuracy and repeatability, and can meet the detection of the Sudan I in the actual sample.
Table 15 recovery of Sudan I from samples
The result shows that the perovskite quantum dot-molecular imprinting fluorescence coding microsphere synthesized by the method not only improves the stability of the perovskite quantum dot, but also utilizes the specific recognition capability of the molecular imprinting polymer to realize the rapid and sensitive quantitative detection of Sudan red I.
Claims (9)
1. A preparation method of perovskite quantum dot-molecular imprinting fluorescent coding microsphere for detecting sudan red I comprises the following steps:
(1) Dissolving sudan red I serving as a template molecule in a pore-forming agent acetonitrile, adding functional monomer methacrylic acid, cross-linking agent ethylene glycol dimethacrylate and divinylbenzene, adding an initiator azodiisobutyronitrile, sealing in nitrogen atmosphere, and stirring and reacting for 24 hours at 60 ℃ to obtain a polymer;
(2) Grinding the polymer, eluting with a mixed solution of methanol and acetic acid by a Soxhlet extraction method, removing template molecules, washing to neutrality by methanol, and drying to constant weight at 60 ℃ to obtain a Sudan red I molecularly imprinted polymer;
(3) Fluorescent coding: adding perovskite quantum dots into n-hexane, carrying out ultrasonic mixing, adding Sudan red I molecularly imprinted polymer, oscillating to combine the quantum dots with the polymer, centrifuging to remove a solvent, washing with n-hexane after the combination is completed, and drying at 25 ℃ to obtain the perovskite quantum dot-molecularly imprinted fluorescent coding microsphere.
2. The preparation method of the perovskite quantum dot-molecularly imprinted fluorescence coding microsphere for detecting sudan red I according to claim 1, wherein the preparation process of the sudan red I molecularly imprinted polymer is as follows:
s1: dissolving 0.1mmol of sudan I in 20mL of acetonitrile, dissolving the sudan I by ultrasonic, adding 4mmol of functional monomer methacrylic acid, 1mmol of cross-linking agent ethylene glycol dimethacrylate and 1mmol of cross-linking agent divinylbenzene, adding 20mg of initiator azodiisobutyronitrile, dissolving the azodiisobutyronitrile by ultrasonic, introducing nitrogen to deoxidize for 15min, and immediately sealing;
s2: heating the polymerization system formed in S1 in water bath for 24 hours at 60 ℃ to obtain an adsorptive polymer;
s3: washing the adsorption polymer with acetonitrile, filtering, putting the adsorption polymer into a 60 ℃ oven for 24 hours, and then, using the volume ratio of 8:2 eluting the mixed solution of methanol and acetic acid in a Soxhlet extraction device, removing Sudan red I template molecules in the absorbent polymer, washing the absorbent polymer to be neutral by using methanol, and drying to constant weight at 60 ℃ to obtain the Sudan red I molecularly imprinted polymer.
3. The method for preparing perovskite quantum dot-molecularly imprinted fluorescence coding microspheres for detecting sudan red I according to claim 1, wherein in (1), divinylbenzene is purified by an alkaline alumina solid phase extraction column.
4. The method for preparing perovskite quantum dot-molecularly imprinted fluorescence encoding microspheres for detecting sudan red I according to claim 1, wherein in (1), the azobisisobutyronitrile is purified by absolute ethanol recrystallization.
5. The method for preparing perovskite quantum dot-molecularly imprinted fluorescent coded microspheres for detecting sudan red i according to claim 1, wherein in (2), the volume ratio of the mixed solution of methanol and acetic acid is 8:2.
6. the method for preparing the perovskite quantum dot-molecular imprinting fluorescent coding microsphere for detecting sudan red I according to claim 1, wherein in the step (3), the fluorescent coding process of the perovskite quantum dot-molecular imprinting fluorescent coding microsphere is as follows:
1mL of n-hexane and 50. Mu.L of 10 mg.mL were added -1 Adding the perovskite quantum dot solution into a 2mL centrifuge tube, carrying out ultrasonic mixing, adding 10mg of Sudan red I molecularly imprinted polymer, carrying out ultrasonic dispersion on the polymer, oscillating for 30min, centrifuging for 10min at 10000rpm, removing supernatant, washing the supernatant with normal hexane until no perovskite quantum dot exists in the supernatant, and drying at 25 ℃ until the weight is constant, thus obtaining the perovskite quantum dot-molecularly imprinted fluorescent coding microsphere.
7. The method for preparing perovskite quantum dot-molecularly imprinted fluorescence encoding microspheres for detecting sudan red I according to claim 1, wherein in (3), the perovskite quantum dot is CsPbBr 3 Quantum dot CsPbCl 1.5 Br 1.5 Quantum dot and CsPbI 2 At least one of the Br quantum dots.
8. The use of the perovskite quantum dot-molecularly imprinted fluorescent coded microsphere according to any one of claims 1-7 for detecting the content of sudan red i in foods.
9. The use of the perovskite quantum dot-molecularly imprinted fluorescent coded microsphere according to any one of claims 1-7 for detecting the content of sudan red i in chilli powder, chilli oil, tomato sauce, chicken eggs and duck eggs.
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